Metal-free epoxidation of alkenes with molecular oxygen and benzaldehyde under visible light irradiation

Synlett

Volumn , Issue 18, 2009, Pages 3024-3026

  Tada, Norihiro ^a   Okubo, Hiroaki ^a   Miura, Tsuyoshi ^a   Itoh, Akichika ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Aerobic; Benzaldehyde; Epoxidation; Visible light

Indexed keywords

ALKENE DERIVATIVE; BENZALDEHYDE; EPOXIDE; OXYGEN;

ARTICLE; EPOXIDATION; FLUORESCENT LIGHTING; IRRADIATION; LIGHT; OXIDATION; SYNTHESIS; VISIBLE LIGHT IRRADIATION;

EID: 72049086959     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218271     Document Type: Article

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32. Exposure of benzaldehyde to the molecular oxygen under visible light irradiation in the presence of trans-stilbene (1) result in the no reaction, probably because trans-stilbene (1) inhibits photooxidation of benzaldehyde. On the other hand, 11% of trans-5-decene oxide was produced when using trans-5-decene instead of 1.
33. Typical Procedure of the Epoxidation A dry MeCN solution (1 mL) of the benzaldehyde (63.7 mg, 0.6 mmol) in a 30 mL round-bottom flask equipped with an O2 balloon was stirred and irradiated with four 22 W fluorescent lamps, which were set up at a distance of 65 mm, for 3 h. The temperature of the final stage of this reaction was about 50 °C. Then, trans-stilbene (1, 54.1 mg, 0.3 mmol) was added to the reaction mixture and stirred without irradiation for 10 h at r.t. The reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC to afford the pure product 2 (52.4 mg, 89%). (8) Yield of perbenzoic acid was determined by integration of 1H NMR with internal standard (1,1,2,2,-tetrachloroethane).